HCID 178523394, compound → HCID 178523983, compound

HRID 1396876Notes

Reaction equation

HRID 1396876 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:36][N:37]([CH:46]=[O:47])[O:38]CC2C=CC=CC=2)[C:8]([N:10]2[CH:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N+:19]=3[O-:25])=[O:16])[CH2:13][CH2:12][N:11]2C(OCC2C=CC=CC=2)=O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[OH-].[OH-].[Pd+2]>[CH:1]1([CH2:6][C@H:7]([CH2:36][N:37]([CH:46]=[O:47])[OH:38])[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N+:19]=3[O-:25])=[O:16])[CH2:13][CH2:12][NH:11]2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 178523394HCID 178523394, compound

Product 1

HCID 178523983HCID 178523983, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl 2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(5-fluoro-1-oxido-2-pyridinyl)amino]carbonyl}-1-pyrazolidinecarboxylate (104 mg, 0.161 mmol) in methanol (4 ml) was added 20% palladium hydroxide on carbon (50 mg, 0.161 mmol). The mixture was hydrogenated under balloon pressure for 1 h and then filtered. The filtrate was purified by reverse-phase HPLC to yield (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-N-(5-fluoro-1-oxido-2-pyridinyl)-3-pyrazolidinecarboxamide (13 mg, 0.028 mmol, 18% yield). LC/MS: (M+H)+: 423.8. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.00-1.27 (m, 2H) 1.39-1.69 (m, 5H) 1.70-1.99 (m, 4H) 2.25-2.45 (m, 1H) 2.45-2.64 (m, 1H) 2.84-3.03 (m, 1H) 3.18-3.30 (m, 1H) 3.53 (dd, J=14.02, 4.42 Hz, 1H) 3.74-3.88 (m, 1H) 3.98 (td, J=9.28, 4.93 Hz, 1H) 4.74-4.87 (m, 1H) 7.37-7.54 (m, 1H) 7.89 (s, 1H) 8.37-8.60 (m, 2H).

Workup

  1. filtrationfiltered
  2. customThe filtrate was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-4d97d8536c5a48e4a0398d31f8e1c26d
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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